Copper compounds of orthooxyazo dyestuffs and a process of making same.



' TUNITEDSTATES- Y BER'IHOLID worn, BERTRKM MAYER, CARL JAGERSPLACHER, Am) EUGENTANDERWERT, or IBASEL, SWITZERLAND, ASSIGNORS TO SOCIETY or CHEMICAL INDUSTRY IN BASLE, F BASEL, .SWI'IZERLAND.

corrira coiuromsnps or oarnooxvazq DYESTUFFS AND A raocnss or MAKING SAME.

1,216,760, I No Drawing- I To all whom it may concern Be it' known that we, Dr. BERTI-IOLD WUTH, chemist, a subject of the King of- Great Britain, Dr. BERTRAM MAYER, chemist,,a subject of the King of Bavaria, Dr,

CARL JAGERSPAOHER, chemist, a'citizen of the Swiss Republic, and EUGEN" ANDERWERT, 'chemist, a citizen of the Swiss Republic, all four residents of Basel, Switzerland, have v invented new-Copper Compounds of Orthooxyazo Dyestuffs and a Process of Making Same, of which the following is a full, clear, and exact. specification.

We have found that the orthooxyazo dyestufl's sensible'to copper can betransformed inwell defined copper compounds soluble in water, from which the copper cannot be precipitated with sodium carbonate, soda lye and ammonia. As these compounds; are o furthermore fast toacids, they suit to dye animal fibers (wool, si-lk, etc), straw, wood.-

bast, etc., in an acid bath. The dyeings produced with these copper products possess a perfect insensibility to copper, a good fastness to washing and particularly an extraordinary fastness to-light, without fur.- ther subsequent treatment.

' The preparation of the new copper compounds is effected by-acting on a watery solution or suspension of the orthooxyazo dyestuffs (either in form of their color acids or in form of the salts of. these latter) with copper compounds as for instance copper salts, copper oxi'd or copper hydroxid.

' Hereby generally-a change of color-occurs.

By a tipping test with potassium ferrocyanid it. can be discerned if thereaction is complete. So far as the copper compounds formed are not directly precipitated 40 from the reaction mass, they'can be-separated by adding common salt.

Example 1: To a solution'of 20 parts of the monoazo dyestufi' derived from orthoamidophenolpara'sulfonic acid and from 2: 5:7-amidonaphtholsulfonic acid in 1000 parts of water is added at 90-to100 the solution of 10 parts copper sulfate. The

coloration ofthe yellow-red solution turns to violet-red. On cooling the coppericompound of the color acid crystallizes in small bright brass-yellow crystals. The compound is separated by filtration, washed with a little water and dried. It constitutes a brown powder with a metallic luster, dissolving in water with a violet-red colora- Application filed August 3, 1915. Serial No. 43,413.

' Specification of Letters Patent. Patented 20, 19 17.

7 tionzwhich does notchange on addition of PATENT-pawn.

soda-lye. From this solution it dyes animal fibers, straw, woodbast, "etc, red-violet tints fast tolwashing and to light. 1 On the other hand the sodium-salt of the monoazo dyestuif employed as parent material dissolves- 111 water with a brownish yellow coloration turning to red-violet on addition of soda lye;it dyes from an acid bath brown tints -ofa lower degree of fastness to washing and to l1ght. The new copper' compound con-- tams.13.31% of copper; 1 Cu in 1 molecule N would correspond to 12.67% Cu.

a solution of 15 parts crystallized copper.

sulfate. The coloration of the red solution Example 2: A'solution of 20 parts of the v turns to dark-cherry-red and the copper compound precipitates from the hot; solution in the form of bright brown needles:

It is separated'by filtration, washed with ia' little water and dried. ,The so obtained 'brown powder: dissolves in water with a.

violet-red coloration which does not change onaddition of soda lye. *From its aqueous solutions it dyes wool, silk, etc., Bordeauxredtints of a very good fastness to light 'ployedfas parent material .or its sodium salt and to washing. The-monoazo dyestuff em- I dissolves in water'withia'n orange-red color- 1 ationturning to violet-red on addition .of

Soda lye-and it dyes in an acid bath.\red

brown tints of a lower degree of fastness to light and washing. J

Example 3: Toya'solution of 20 of the monoazo dyestuif derived from sulfoam-' idosalicylic' acid and phenylmethylpyra: zolone in 500 parts of boiling. wateris added a solution of 12 parts-copper sulfate.

The orange coloration of the solution turns to brown and on cooling the copper compound separates asorangebrown small nee-' dles. After filtering, washing and drying it constitutes an'orange powder, dissolving in water with a brown-yellow colorationwhich.

does not change on addition of soda lye.

-Copper compound of the dyestufi resulting from D ein from the diazo denvat1ve S g on 'wool, silk, v straw, etc.

NH; Alpha-11a hthol...Q.... Pure-violet. Beta-nap tho] Violet. 1-Pheny1-3-methyl-5- Blue-red. pyrazolone.

EiO H NH, Alpha-1.1a hthol Pui'e-violet; v Beta nap thol Violet. 15 l-PhenyLB-methyl-5- Bluered.

- I I pyrezolone.

(iH SO H NH, Alpha-naphtholhh'nn Dw? blne-vio-- 1-Phenj/l-3-methyl-5- -pyrazolone.

Blue-red.

transformed into lac-dyes What we claim is: 1. The herein described process for the nesses.

' manufacture of new copper compoundsoof orthooxyazo dyestuffs, soluble in water, consisting in acting with acopper compound onorthoox-yazo dyestuffs sensible to copper in the presence of a solvent.

' 2. As new products the'described new'copper compounds of orthooxyazo dyestuffs, which are soluble in water, from which the copper cannot be precipitated with Sodium carbonate, soda lye and ammonia and which constitute powders of metallic luster dis- 'stufiFs, various tints showing without any further treatmenta very good fastness-to v washing and to light;

In witness whereof we have hereunto slgned our names this 15th day of July, 1915, in the presence of two subscribing wit- DR. BERTHOLD WUTH.

DR. BERTRAM MAYER. Y DR. "CARL JAGERSPACHEB. EUGEN ANDERWERT. Witnesses; i

' ARNono ZUBER, v

AMAND R 'i'mn. 

